title: HClO4 x SiO2 catalysed synthesis of alkyl 3-deoxy-hex-2-enopyranosides from 2-hydroxy glucal ester: application in the synthesis of a cis-fused bicyclic ether and a 4-amino-C-glucoside.
abstract: A variety of alcohols react with 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabino-hex-1-enopyranose 1 in the presence of a catalytic amount of HClO(4) supported on silica gel to give the corresponding alkyl 3-deoxy-hex-2-enopyranosides 2 in high yield, with short reaction times (10-45 mins) and good alpha-selectivity. Work-up merely involves filtration of the reagent, followed by chromatographic purification of the crude product. This methodology has also been employed in the synthesis of a bicyclic ether, a useful precursor for cyclic polyethers, and a 4-amino-C-glucoside.
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Kanpur 208 016, India.
authors.forename: Preeti
authors.initials: P
authors.lastname: Gupta
authors.forename: Nitee
authors.initials: N
authors.lastname: Kumari
authors.forename: Aditi
authors.initials: A
authors.lastname: Agarwal
authors.forename: Yashwant D
authors.initials: YD
authors.lastname: Vankar